So a couple weeks ago (episode 5?), Tommy (played by Denis Leary, who's a super macho firefighter) gets so shit-faced that the girl he meets decides that since he's so boring and can't really perform, that she'd have a little fun with him and dress him up. The really interesting thing is I believe Leary is the creator/writer/producer of the show. So either he's sorta secretly into crossdressing, or he thinks the most fucked up thing you could end up doing while drunk is crossdressing?
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"Tommy, you remember what I did to you last night?"
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"Can't say that I do, I was really drunk last night"
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"oooh ho ho ho! These pictures are priceless!"
"Let me see!"
"Nice earrings there tommy!"
"Looks like you liked the bra too!"
"Ahhhh! ha ha ha! I am so putting these on my facebook page!"
"Glad I was able to entertain you"